Cottage holiday rentals in Winchester

Find and book unique cottages on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for cottage rentals in Winchester

Cottage rentals with a hot tub

Superhost
Cottage in Harpers Ferry
4.85 out of 5 average rating, 184 reviews

Wild & Cozy | Harpers Ferry Mountain Escape

KevinRating, 5 stars2 weeks ago
Good quiet place to stay near Harper’s Ferry. Place was clean, hot tub was nice we were able to watch deer next door and across the street hang out and graze. Everything was in place and clean. Beds were soft and comfortable. The only issue that I have is the rocks that line the driveway especially when turning out of the driveway will catch lower vehicles and cars it caused a little damage to my wife’s car and be careful where you park there is an oak tree with dead and rotting limbs that need to be trimmed that are right above the area where cars would park if you have more than one car. If I were to ever come back to Harper’s Ferry I would definitely stay there again.
Top guest favourite
Cottage in Luray
4.97 out of 5 average rating, 369 reviews

Holly Tree Retreat Located In Beautiful Luray, VA.

MatthewRating, 5 stars1 week ago
From the first step inside, felt right at home. Fully stocked kitchen and the place was spotless. Definitely a 10 out of 10. Was a bonus having such an amazing view of the mountains and cows. Do yourself a favor and book this location!
Top guest favourite
Cottage in Berkeley Springs
4.95 out of 5 average rating, 147 reviews

Cozy Cottage in the heart of Berkeley Springs WV

DeborahRating, 5 stars6 days ago
Elizabeth Cottage is an absolute gem! The home is cozy, comfortable, and filled with sweet touches that made our stay lovely. The yard is large and so pretty, with nice outdoor seating spaces to enjoy the garden and birds. We loved being so close to the springs, baths, and shopping. Everything inside was top notch and completely ready for our arrival. Thank you for sharing your beautiful home with us!
Superhost
Cottage in Luray
4.84 out of 5 average rating, 103 reviews

Creekside Cottage at Shenandoah

JohnRating, 5 stars4 weeks ago
We had a fantastic time and would recommend to everyone! It’s a beautiful place, very quiet and really close to the national park.
Guest favourite
Cottage in Stanley
4.87 out of 5 average rating, 142 reviews

Vibrant Cottage | Hot Tub | Pets | Shenandoah NP

KelseyRating, 5 stars6 days ago
We had a great stay! Olivia was an excellent host. The place had the perfect vibe for a girls weekend and birthday celebration. The only issue we had was needing to catch 2 wasps that were in the house, but we were able to take care of that without issue. It was so nice to have so many towels and amenities that you don’t normally have in an Airbnb. Thanks again!
Guest favourite
Cottage in Capon Bridge
4.97 out of 5 average rating, 181 reviews

The 3R's River, Relaxation, Retreat + hot tub

SantiagoRating, 5 stars6 days ago
Darrel went above and beyond in making sure we had a great stay! He was kind, responsive and overall a superstar. We had an incredibly relaxing time and enjoyed the peace his listing had to offer. An EXCELLENT way to spend some time away from the city. I hope to come back soon! Couldn't be happier with Darrel's service!
Guest favourite
Cottage in Berkeley Springs
4.95 out of 5 average rating, 442 reviews

Hidden Hill - Cozy Downtown Cottage with Hot Tub!!

MicheleRating, 5 stars2 weeks ago
So comfy and clean! Stayed for a few nights with some friends to forget about life for awhile. Easy walk to town, awesome hot tub on the deck and the grill works great. We left recharged and will def be back!
Top guest favourite
Cottage in Winchester
4.99 out of 5 average rating, 396 reviews

Uber SXY Private Country Escape! Hot Tub & Views~

DorothyRating, 5 stars3 days ago
FOXY was a pure delight! Just book it and you can enjoy the trendy decor, well stocked modern kitchen, comfiest bed, squeaky clean oversized bathroom, and serene views of the rolling hills (and mountains in the background) with cattle and sheep grazing in the distance. You might also get the bonus of enjoying a star-filled evening from the private hot tub just steps away from the side door! There’s plenty of great restaurants , shopping, and activities nearby but pack your bags and enjoy your retreat! Gillian is a most attentive host, check in and check out was a breeze, and the house instruction/guide book was easy to use and helpful. Attention was given to every detail to make guests feel welcome, comfortable, and spoiled!

Pet-friendly cottage rentals

Top guest favourite
Cottage in Greencastle
4.96 out of 5 average rating, 103 reviews

Cozytown Cottage/Whitetail Ski Resort/Hagerstown

KimberlyRating, 5 stars3 days ago
Jen's place never disappoints. Peaceful and secluded but close to so many things for entertainment if thats what you want. I enjoyed just settling back and relaxing.
Superhost
Cottage in Hamilton
4.87 out of 5 average rating, 397 reviews

Robins Nest

JordanRating, 5 stars1 week ago
We had a wonderful stay! The property was a great deal and exactly what we were looking for — peaceful, private, and secluded without being too far from everything. The location was perfect for a relaxing getaway. The host was incredibly friendly, responsive, and proactive, which made the whole experience even better. The listing description was accurate, everything was spotlessly clean, the AC worked perfectly, and check-in was super easy. We would absolutely stay here again and highly recommend it to anyone looking for a quiet, comfortable place to stay!
Top guest favourite
Cottage in New Market
4.95 out of 5 average rating, 132 reviews

The willow tree house

GenineRating, 5 stars1 week ago
Susan’s place was full of thoughtful touches like wireless phone chargers, a basket of various charging cables and even some Easter treats and a smores “kit” to use at the fire pit. Perfectly situated for a visit to Luray Caverns and Shenandoah National Park. Great hot showers, fluffy towels and comfy beds. Well equipped kitchen and outdoor deck area for outside dining, with gas grill were appreciated. We thoroughly enjoyed our stay!
Top guest favourite
Cottage in Mathias
4.93 out of 5 average rating, 191 reviews

Lost River Dog/Bike friendly 3BR/2BA-large deck

ChrisRating, 5 stars1 month ago
The cottage/house was as described and wonderful. The location was perfect to explore the many nearby hiking and outdoors options. The property itself has an excellent view. The fenced in yard was convenient for our dog. Inside everything was clean and well-maintained. There were a number of nice touches to make you feel at home. There was everything one would need and more. I needed to work remotely one day and the WiFi was very reliable. Great stay!
Guest favourite
Cottage in Luray
4.94 out of 5 average rating, 110 reviews

Sweet Scenes Cottage

TaylorRating, 5 stars6 days ago
We had a great stay! This is the CLEANEST Airbnb I’ve ever been to. Very beautiful area and scenery, and perfect distance from Luray Caverns and Shenandoah National Park. Valerie was very responsive and helpful when needed. The only suggestion would be to take a car that can handle a somewhat steep and rocky driveway.
Top guest favourite
Cottage in Etlan
4.98 out of 5 average rating, 183 reviews

Amy's Place

DixieRating, 5 stars6 days ago
This was our third time staying here and it is always wonderful. The property itself is beautiful and peaceful. Our dog loves the fenced in yard and dog amenities (water bowl, poop bags). The coffee that Billy provides is so good and much appreciated. Phone coverage can be spotty (the provide wifi works great), so the recommendations and directions provided in the Welcome binder are very useful. Love it here & hoping we will be able to visit again soon.
Top guest favourite
Cottage in Fort Valley
4.96 out of 5 average rating, 208 reviews

Cozy Cottage/Pet Heaven

AnnaRating, 5 stars5 days ago
We had a lot of fun on our weekend getaway! The land is absolutely breathtaking and the house was impeccably clean. The cows are such a joy. When the cows are in the closest pasture, they share a fence with you. My dogs were startled at first.
Guest favourite
Cottage in Purcellville
4.83 out of 5 average rating, 209 reviews

Stone School House - Minutes from Harper's Ferry

KatieRating, 5 stars2 weeks ago
Mark’s place was perfect! It was just what our family of four needed for a last-minute getaway. The house is beautiful and unique and we appreciated the basket of goodies. Location’s convenient to Harper’s Ferry, Charles Town, Frederick, Shepherdstown. My husband loved the sauna! Mark was super kind and responsive. We had a wonderful stay!

Private cottage rentals

Top guest favourite
Cottage in Bridgewater
5 out of 5 average rating, 20 reviews

Charming riverside cottage-firepit, yard, Pets

KurtRating, 5 stars1 week ago
The house was great for our group. We really enjoyed sitting out on the patio. It was hot when we were there and the AC worked well. We put in our kayak right from the back yard and enjoyed paddling on the river. It was an easy walk to Main Street and Bridgewater College. We will definitely look to book again if we are back in the Bridgewater area.
Guest favourite
Cottage in Star Tannery
5 out of 5 average rating, 9 reviews

Cottage w/EV Charger + Trout Stream

BrianRating, 5 stars3 months ago
WE had a lovely weekend stay at Bret's place. It was a cold, snowy trip but we still took long walks up the road and watched the snow fall with a roaring fire. Bret did a good job reaching out to make sure everything went smoothly. The kitchen is quite small but has everything you need to cook some good meals. Would be a cool place to visit in warmer months with the lovely creek right outside the front door! Do note the water is pretty smelly so you can do everything with it but drink, but there is plenty of drinking water provided.
Guest favourite
Cottage in Purcellville
4.93 out of 5 average rating, 82 reviews

Beautiful 3 bedroom cottage on 15 private acres.

JakeRating, 5 stars1 week ago
Very nice space with all the accommodations you could want. Very well clean and comfortable. Throughly enjoyed our stay.
Top guest favourite
Cottage in Mercersburg
5 out of 5 average rating, 31 reviews

Purple Kangaroo Cottages

SamRating, 5 stars2 months ago
We had a lovely stay at this cottage. Very clean and nice amenities. 25 minutes from White tail and 15 minutes from downtown Mercersburg. Super friendly hosts.
Top guest favourite
Cottage in Bluemont
5 out of 5 average rating, 122 reviews

Snickers Gap Cottage

SuzanneRating, 5 stars6 days ago
I’d give it 6 stars if I could! Over the top wonderful weekend. The chocolate chip cookies were delicious! The charm of this cozy cottage was perfect. And no over the top rules! Everything made sense. Truly enjoyed our stay. And so many beautiful vineyards in the area!
Top guest favourite
Cottage in Madison
4.94 out of 5 average rating, 87 reviews

Spectacular Mountain Retreat

BriannaRating, 5 stars1 month ago
This place was perfect for our weekend getaway. The cabin was spacious, clean and comfortable, plus close to so many hikes in Shenandoah national park. The hosts really thought of everything, from coffee to cookware and even having the fire pit filled with brush so we could easily have a fire. The location is nestled in the mountainside and is SO quiet, coffee overlooking the mountains and hills with nothing but the sounds of nature was therapeutic. We are already talking about planning our next trip back!
Guest favourite
Cottage in Waterford
4.97 out of 5 average rating, 126 reviews

Wheatland Spring Farm + Brewery Cottage House

RachelRating, 5 stars2 weeks ago
My husband and I decided on a last-minute weekend getaway, and Bonnie was so accommodating with this gorgeous little cottage! The space was clean, comfortable, thoughtfully furnished, and the kitchen had everything we needed. The historical details were one-of-a-kind. Absolutely loved the quiet setting on the family farm and close proximity to the brewery, too! I would highly recommend this space - it's the perfect location for exploring wine country.
Superhost
Cottage in Knoxville
4.71 out of 5 average rating, 113 reviews

Rustic Cottage near Historic Harper's Ferry!

Zack and CarolynRating, 5 stars2 weeks ago
My children loved the upstairs loft which even had a toilet and sink! The couch was cozy, the beds were comfortable, the kitchen had the basics, Joe and his co-hosts were responsive, and we enjoyed using the house as a base camp to explore fishing at the hatchery and going to Harper's Ferry. Thank you!

Destinations to explore

  1. Airbnb
  2. United States
  3. Virginia
  4. Winchester
  5. Cottage rentals